Adenosine‐mediated Photoreaction of 4,5′,8‐trimethylpsoralen With Alcohols

Yun, Mi Hong; Choi, Seung Ju; Shim, Sang Chul

doi:10.1111/j.1751-1097.1993.tb09543.x

Cited by 1 publication

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“…Recently, Shim et al suggested that the photoreaction of psoralen with DNA proceeds by adenosine-mediated electron transfer from/to psoralen to/from thymine base. 17,18 Moreover, they reported that the poly[dA-dT]⋅poly[dA-dT] sequence region is the most favorable site for the photocycloaddition reactions of furocoumarins. 17 Because of the importance of interaction between the 8-methosypsoralen and purine base pairs in DNA, we prepared some model § Dedicated to Professor Sang Chul Shim for his distinguished achievements in chemistry and outstanding contributions to the Korea Chemical Society.…”

Section: Introductionmentioning

confidence: 99%

Photohysical Properties of New Psoralen Derivatives:Psoralens Linked to Adenine through Polymethylene Chains

Yoo¹,

Park

Kim³

et al. 2002

Bulletin of the Korean Chemical Society

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The model compounds, 8-methoxypsoralen-CH2O(CH2)n-adenine (MOPCH2OCnAd, n=2, 3, 5, 6, 8, and 10) in which 5 position of 8-methoxypsoralen (8-MOP) is linked by various lengths of polymethylene bridge to N 9 of adenine. UV absorption spectra are identical with the sum of MOPCH2OC3 and adenine absorption spectra. Solvent effects on the UV absorption and fluorescence emission spectra indicate that the lowest excited singlet state is the (π→π*) state. The spectral characteristics of the fluorescence of MOPCH2OCnAd are strongly dependent upon the nature of the solvents. The fluorescence emission spectra in aprotic solvents are broad and structureless due to the excimer formation through the folded conformation accelerated by hydrophobic π-π stacking interaction. Increasing polarity of the protic solvents leads to higher population of unfolded conformation stabilized through favorable solvation and H-bonding, and consequently to an increase in the fluorescence intensity, fluorescence lifetime, and a shift of fluorescence maximum to longer wavelengths. The decay characteristics of the fluorescence in polar protic solvents shows two exponential decays with the lifetimes of 0.6-0.8 and 1.6-1.9 ns in 5% ethanol/water, while MOPCH2OC3 shows 0.5 and 1.7 ns fluorescence lifetimes. The long-lived component of fluorescence can be attributed to the relaxed species (i.e., the species for which the solvent reorientation (or relaxation) has occurred), while the short-lived components can be associated with the unrelaxed, or only partially relaxed, species.

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Section: Introductionmentioning

confidence: 99%